({[({[(2R,3R,5R)-5-{4-amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(sulfanylidene)phosphonous acid

• ChemBase ID: 159843
• Molecular Formular: C17H22N5O12P3S
• Molecular Mass: 613.369163
• Monoisotopic Mass: 613.01985206
• SMILES: n1cnc2c(c1N)c(nn2[C@H]1C([C@H]([C@H](O1)COP(=O)(OP(=O)(O)OP(=S)(O)O)O)O)O)Cc1ccccc1
• Canonical SMILES: OC1[C@@H](O)[C@H](O[C@H]1n1nc(c2c1ncnc2N)Cc1ccccc1)COP(=O)(OP(=O)(OP(=S)(O)O)O)O
• InChI: InChI=1S/C17H22N5O12P3S/c18-15-12-10(6-9-4-2-1-3-5-9)21-22(16(12)20-8-19-15)17-14(24)13(23)11(32-17)7-31-35(25,26)33-36(27,28)34-37(29,30)38/h1-5,8,11,13-14,17,23-24H,6-7H2,(H,25,26)(H,27,28)(H2,18,19,20)(H2,29,30,38)/t11-,13+,14?,17-/m1/s1
• InChIKey: HXCICTJXZYTSMD-NUKIEUHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3R,5R)-5-{4-amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(sulfanylidene)phosphonous acid
• IUPAC Traditional name: ({[(2R,3R,5R)-5-{4-amino-3-benzylpyrazolo[3,4-d]pyrimidin-1-yl}-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(sulfanylidene)phosphonous acid
• Synonyms: 4-Amino-3-benzyl-1H-pyrazolo[3,4-d]pyrimidine 1-β-D-Ribofuranosyl 5'-(3-Thio- triphosphate)

Database IDs

• PubChem SID: 162253978
• PubChem CID: 71313156

CALCULATED PROPERTIES

• Acid pKa: 1.0290473
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -7.751111
• LogD (pH = 7.4): -8.677913
• Log P: -2.5412054
• Molar Refractivity: 144.5425 cm^3
• Polarizability: 52.826267 Å^3
• Polar Surface Area: 262.06 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A600270

Used in the synthesis of nucleotide analogues containing a phosphorothiolate moiety at the terminal position of the phospate chain.

REFERENCES

• Sun, I., et al.: J. Biol. Chem., 255, 742 (1980)
• Merwe, P.A., et al.: Biochem. J., et al.: 275, 399 (1980)